Acid - Wikipedia, The Free Encyclopedia

8/8/2014 Acid - Wikipedia, the free encyclopedia
http://en.wikipedia.org/wiki/Acid 1/12
Zinc, a typical metal, reacting with
hydrochloric acid, a typical acid
Acid
From Wikipedia, the free encyclopedia
An acid (from the Latin acidus/acre meaning sour
[1]
) is a chemical
substance whose aqueous solutions are characterized by a sour taste,
the ability to turn blue litmus red, and the ability to react with bases
and certain metals (like calcium) to form salts. Aqueous solutions of
acids have a pH of less than 7. A lower pH means a higher acidity,
and thus a higher concentration of positive hydrogen ions in the
solution. Chemicals or substances having the property of an acid are
said to be acidic.
Common examples of acids include hydrochloric acid (a solution of
hydrogen chloride which is found in gastric acid in the stomach and
activates digestive enzymes), acetic acid (vinegar is a dilute solution of
this liquid), sulfuric acid (used in car batteries), and tartaric acid (a
solid used in baking). As these examples show, acids can be solutions
or pure substances, and can be derived from solids, liquids, or gases.
Strong acids and some concentrated weak acids are corrosive, but there are exceptions such as carboranes and
boric acid.
There are three common definitions for acids: the Arrhenius definition, the Brnsted-Lowry definition, and the
Lewis definition. The Arrhenius definition defines acids as substances which increase the concentration of
hydrogen ions (H
+
), or more accurately, hydronium ions (H
3
O
+
), when dissolved in water. The Brnsted-
Lowry definition is an expansion: an acid is a substance which can act as a proton donor. By this definition, any
compound which can easily be deprotonated can be considered an acid. Examples include alcohols and amines
which contain O-H or N-H fragments. A Lewis acid is a substance that can accept a pair of electrons to form a
covalent bond. Examples of Lewis acids include all metal cations, and electron-deficient molecules such as
boron trifluoride and aluminium trichloride.
Contents
1 Definitions and concepts
1.1 Arrhenius acids
1.2 Brnsted-Lowry acids
1.3 Lewis acids
2 Dissociation and equilibrium
3 Nomenclature
4 Acid strength
5 Chemical characteristics
5.1 Monoprotic acids
5.2 Polyprotic acids
5.3 Neutralization
5.4 Weak acidweak base equilibrium
Svante Arrhenius
6 Applications of acids
6.1 Acid catalysis
7 Biological occurrence
8 Common acids
8.1 Mineral acids (inorganic acids)
8.2 Sulfonic acids
8.3 Carboxylic acids
8.4 Halogenated carboxylic acids
8.5 Vinylogous carboxylic acids
8.6 Nucleic acids
9 References
10 External links
Definitions and concepts
Modern definitions are concerned with the fundamental chemical reactions common to all acids.
Most acids encountered in everyday life are aqueous solutions, or can be dissolved in water, so the Arrhenius
and Brnsted-Lowry definitions are the most relevant.
The Brnsted-Lowry definition is the most widely used definition; unless otherwise specified, acid-base
reactions are assumed to involve the transfer of a proton (H
+
) from an acid to a base.
Hydronium ions are acids according to all three definitions. Interestingly, although alcohols and amines can be
Brnsted-Lowry acids, they can also function as Lewis bases due to the lone pairs of electrons on their oxygen
and nitrogen atoms.
Arrhenius acids
The Swedish chemist Svante Arrhenius attributed the properties of acidity to
hydrogen ions (H
+
) or protons in 1884. An Arrhenius acid is a substance that,
when added to water, increases the concentration of H
+
ions in the water. Note
that chemists often write H
+
(aq) and refer to the hydrogen ion when describing
acid-base reactions but the free hydrogen nucleus, a proton, does not exist alone
in water, it exists as the hydronium ion, H
3
O
+
. Thus, an Arrhenius acid can also
be described as a substance that increases the concentration of hydronium ions
when added to water. This definition stems from the equilibrium dissociation of
water into hydronium and hydroxide (OH
) ions:
[2]
H
2
O
(l)
+ H
2
O
(l)
H
3
O
+
(aq)
+ OH
(aq)
Acetic acid, a weak acid, donates a proton (hydrogen ion,
highlighted in green) to water in an equilibrium reaction to
give the acetate ion and the hydronium ion. Red: oxygen,
black: carbon, white: hydrogen.
In pure water the majority of molecules are H
2
O, but the molecules are constantly dissociating and re-
associating, and at any time a small number of the molecules (always near 1 in 10
7
) are hydronium and an equal
number are hydroxide. Because the numbers are equal, pure water is neutral (not acidic or basic).
An Arrhenius base, on the other hand, is a substance which increases the concentration of hydroxide ions when
dissolved in water, hence decreasing the concentration of hydronium.
The constant association and disassociation of H
2
O molecules forms an equilibrium in which any increase in the
concentration of hydronium is accompanied by a decrease in the concentration of hydroxide, thus an Arrhenius
acid could also be said to be one that decreases hydroxide concentration, with an Arrhenius base increasing it.
The reason that pHs of acids are less than 7 is that the concentration of hydronium ions is greater than 10
7
moles per liter. Since pH is defined as the negative logarithm of the concentration of hydronium ions, acids thus
have pHs of less than 7.
Brnsted-Lowry acids
While the Arrhenius concept is useful for
describing many reactions, it is also quite limited
in its scope. In 1923 chemists Johannes
Nicolaus Brnsted and Thomas Martin Lowry
independently recognized that acid-base
reactions involve the transfer of a proton. A
Brnsted-Lowry acid (or simply Brnsted
acid) is a species that donates a proton to a
Brnsted-Lowry base.
[2]
Brnsted-Lowry
acid-base theory has several advantages over
Arrhenius theory. Consider the following
reactions of acetic acid (CH
3
COOH), the organic acid that gives vinegar its characteristic taste:
CH
3
COOH + H
2
O CH
3
COO
+ H
3
O
+
CH
3
COOH + NH
3
CH
3
COO
+ NH
+
4
Both theories easily describe the first reaction: CH
3
COOH acts as an Arrhenius acid because it acts as a source
of H
3
O
+
when dissolved in water, and it acts as a Brnsted acid by donating a proton to water. In the second
example CH
3
COOH undergoes the same transformation, in this case donating a proton to ammonia (NH
3
), but
cannot be described using the Arrhenius definition of an acid because the reaction does not produce hydronium.
Brnsted-Lowry theory can also be used to describe molecular compounds, whereas Arrhenius acids must be
ionic compounds. Hydrogen chloride (HCl) and ammonia combine under several different conditions to form
ammonium chloride, NH
4
Cl. In aqueous solution HCl behaves as hydrochloric acid and exists as hydronium and
chloride ions. The following reactions illustrate the limitations of Arrhenius's definition:
1. H
3
O
+
(aq)
+ Cl
(aq)
+ NH
3
Cl
(aq)
+ NH
4
+
(aq)
+ H
2
O
2. HCl
(benzene)
+ NH
3(benzene)
NH
4
Cl
(s)
3. HCl
(g)
+ NH
3(g)
NH
4
Cl
(s)
As with the acetic acid reactions, both definitions work for the first example, where water is the solvent and
hydronium ion is formed by the HCl solute. The next two reactions do not involve the formation of ions but are
still proton transfer reactions. In the second reaction hydrogen chloride and ammonia (dissolved in benzene)
react to form solid ammonium chloride in a benzene solvent and in the third gaseous HCl and NH
3
combine to
form the solid.
Lewis acids
A third concept was proposed in 1923 by Gilbert N. Lewis which includes reactions with acid-base
characteristics that do not involve a proton transfer. A Lewis acid is a species that accepts a pair of electrons
from another species; in other words, it is an electron pair acceptor.
[2]
Brnsted acid-base reactions are proton
transfer reactions while Lewis acid-base reactions are electron pair transfers. All Brnsted acids are also Lewis
acids, but not all Lewis acids are Brnsted acids. Contrast the following reactions which could be described in
terms of acid-base chemistry.
In the first reaction a fluoride ion, F
, gives up an electron pair to boron trifluoride to form the product

tetrafluoroborate. Fluoride "loses" a pair of valence electrons because the electrons shared in the BF bond
are located in the region of space between the two atomic nuclei and are therefore more distant from the fluoride
nucleus than they are in the lone fluoride ion. BF
3
is a Lewis acid because it accepts the electron pair from
fluoride. This reaction cannot be described in terms of Brnsted theory because there is no proton transfer. The
second reaction can be described using either theory. A proton is transferred from an unspecified Brnsted acid
to ammonia, a Brnsted base; alternatively, ammonia acts as a Lewis base and transfers a lone pair of electrons
to form a bond with a hydrogen ion. The species that gains the electron pair is the Lewis acid; for example, the
oxygen atom in H
3
O
+
gains a pair of electrons when one of the HO bonds is broken and the electrons shared
in the bond become localized on oxygen. Depending on the context, a Lewis acid may also be described as an
oxidizer or an electrophile.
Dissociation and equilibrium
Reactions of acids are often generalized in the form HA H
+
+ A
, where HA represents the acid and A
is
the conjugate base. Acid-base conjugate pairs differ by one proton, and can be interconverted by the addition
or removal of a proton (protonation and deprotonation, respectively). Note that the acid can be the charged
species and the conjugate base can be neutral in which case the generalized reaction scheme could be written as
HA
+
H
+
+ A. In solution there exists an equilibrium between the acid and its conjugate base. The equilibrium
constant K is an expression of the equilibrium concentrations of the molecules or the ions in solution. Brackets
indicate concentration, such that [H
2
O] means the concentration of H
2
O. The acid dissociation constant K
a
is
generally used in the context of acid-base reactions. The numerical value of K
a
is equal to the product of the
concentrations of the products divided by the concentration of the reactants, where the reactant is the acid (HA)
and the products are the conjugate base and H
+
.
The stronger of two acids will have a higher K
a
than the weaker acid; the ratio of hydrogen ions to acid will be
higher for the stronger acid as the stronger acid has a greater tendency to lose its proton. Because the range of
possible values for K
a
spans many orders of magnitude, a more manageable constant, pK
a
is more frequently
used, where pK
a
= -log
10
K
a
. Stronger acids have a smaller pK
a
than weaker acids. Experimentally determined
pK
a
at 25 C in aqueous solution are often quoted in textbooks and reference material.
Nomenclature
In the classical naming system, acids are named according to their anions. That ionic suffix is dropped and
replaced with a new suffix (and sometimes prefix), according to the table below. For example, HCl has chloride
as its anion, so the -ide suffix makes it take the form hydrochloric acid. In the IUPAC naming system, "aqueous"
is simply added to the name of the ionic compound. Thus, for hydrogen chloride, the IUPAC name would be
aqueous hydrogen chloride. The prefix "hydro-" is added only if the acid is made up of just hydrogen and one
other element.
Classical naming system:
Anion prefix Anion suffix Acid prefix Acid suffix Example
per ate per ic acid perchloric acid (HClO
4
)
ate ic acid chloric acid (HClO
3
)
ite ous acid chlorous acid (HClO
2
)
hypo ite hypo ous acid hypochlorous acid (HClO)
ide hydro ic acid hydrochloric acid (HCl)
Acid strength
The strength of an acid refers to its ability or tendency to lose a proton. A strong acid is one that completely
dissociates in water; in other words, one mole of a strong acid HA dissolves in water yielding one mole of H
+
and one mole of the conjugate base, A
, and none of the protonated acid HA. In contrast, a weak acid only
partially dissociates and at equilibrium both the acid and the conjugate base are in solution. Examples of strong
acids are hydrochloric acid (HCl), hydroiodic acid (HI), hydrobromic acid (HBr), perchloric acid (HClO
4
),
nitric acid (HNO
3
) and sulfuric acid (H
2
SO
4
). In water each of these essentially ionizes 100%. The stronger an
acid is, the more easily it loses a proton, H
+
. Two key factors that contribute to the ease of deprotonation are
the polarity of the HA bond and the size of atom A, which determines the strength of the HA bond. Acid
strengths are also often discussed in terms of the stability of the conjugate base.
Stronger acids have a larger K
a
and a more negative pK
a
than weaker acids.
Sulfonic acids, which are organic oxyacids, are a class of strong acids. A common example is toluenesulfonic
acid (tosylic acid). Unlike sulfuric acid itself, sulfonic acids can be solids. In fact, polystyrene functionalized into
polystyrene sulfonate is a solid strongly acidic plastic that is filterable.
Superacids are acids stronger than 100% sulfuric acid. Examples of superacids are fluoroantimonic acid, magic
acid and perchloric acid. Superacids can permanently protonate water to give ionic, crystalline hydronium
"salts". They can also quantitatively stabilize carbocations.
While K
a
measures the strength of an acid compound, the strength of an aqueous acid solution is measured by
pH, which is an indication of the concentration of hydronium in the solution. The pH of a simple solution of an
acid compound in water is determined by the dilution of the compound and the compound's K
a
.
Chemical characteristics
Monoprotic acids
Monoprotic acids are those acids that are able to donate one proton per molecule during the process of
dissociation (sometimes called ionization) as shown below (symbolized by HA):
HA
(aq)
+ H
2
O
(l)
H
3
O
+
(aq)
+ A
(aq)
K
a
Common examples of monoprotic acids in mineral acids include hydrochloric acid (HCl) and nitric acid
(HNO
3
). On the other hand, for organic acids the term mainly indicates the presence of one carboxylic acid
group and sometimes these acids are known as monocarboxylic acid. Examples in organic acids include formic
acid (HCOOH), acetic acid (CH
3
COOH) and benzoic acid (C
6
H
5
COOH).
Polyprotic acids
Polyprotic acids, also known as polybasic acids, are able to donate more than one proton per acid molecule, in
contrast to monoprotic acids that only donate one proton per molecule. Specific types of polyprotic acids have
more specific names, such as diprotic acid (two potential protons to donate) and triprotic acid (three potential
protons to donate).
A diprotic acid (here symbolized by H
2
A) can undergo one or two dissociations depending on the pH. Each
dissociation has its own dissociation constant, K
a1
and K
a2
.
H
2
A
(aq)
+ H
2
O
(l)
H
3
O
+
(aq)
+ HA
(aq)
K
a1
HA
(aq)
+ H
2
O
(l)
H
3
O
+
(aq)
+ A
2
(aq)
K
a2
The first dissociation constant is typically greater than the second; i.e., K
a1
> K
a2
. For example, sulfuric acid
(H
2
SO
4
) can donate one proton to form the bisulfate anion (HSO
4
), for which K
a1
is very large; then it can
donate a second proton to form the sulfate anion (SO
4
2-
), wherein the K
a2
is intermediate strength. The large
K
a1
for the first dissociation makes sulfuric a strong acid. In a similar manner, the weak unstable carbonic acid
(H
2
CO
3
) can lose one proton to form bicarbonate anion (HCO
3
) and lose a second to form carbonate anion

(CO
3
2-
). Both K
a
values are small, but K
a1
> K
a2
.
A triprotic acid (H
3
A) can undergo one, two, or three dissociations and has three dissociation constants, where
K
a1
> K
a2
> K
a3
.
H
3
A
(aq)
+ H
2
O
(l)
H
3
O
+
(aq)
+ H
2
A
(aq)
K
a1
H
2
A
(aq)
+ H
2
O
(l)
H
3
O
+
(aq)
+ HA
2
(aq)
K
a2
HA
2
(aq)
+ H
2
O
(l)
H
3
O
+
(aq)
+ A
3
(aq)
K
a3
An inorganic example of a triprotic acid is orthophosphoric acid (H
3
PO
4
), usually just called phosphoric acid.
All three protons can be successively lost to yield H
2
PO
4
, then HPO
4
2-
, and finally PO
4
3-
, the orthophosphate
ion, usually just called phosphate. An organic example of a triprotic acid is citric acid, which can successively
lose three protons to finally form the citrate ion. Even though the positions of the protons on the original molecule
may be equivalent, the successive K
a
values will differ since it is energetically less favorable to lose a proton if
the conjugate base is more negatively charged.
Although the subsequent loss of each hydrogen ion is less favorable, all of the conjugate bases are present in
solution. The fractional concentration, (alpha), for each species can be calculated. For example, a generic
diprotic acid will generate 3 species in solution: H
2
A, HA
-
, and A
2-
. The fractional concentrations can be
calculated as below when given either the pH (which can be converted to the [H
+
]) or the concentrations of the
acid with all its conjugate bases:
A plot of these fractional concentrations against pH, for given K
1
and K
2
, is known as a Bjerrum plot. A pattern
is observed in the above equations and can be expanded to the general n -protic acid that has been
deprotonated i -times:
where K
0
= 1 and the other K-terms are the dissociation constants for the acid.
Neutralization
Hydrochloric acid (in beaker) reacting
with ammonia fumes to produce
ammonium chloride (white smoke).
Neutralization is the reaction between an acid and a base, producing a
salt and neutralized base; for example, hydrochloric acid and sodium
hydroxide form sodium chloride and water:
HCl
(aq)
+ NaOH
(aq)
H
2
O
(l)
+ NaCl
(aq)
Neutralization is the basis of titration, where a pH indicator shows
equivalence point when the equivalent number of moles of a base
have been added to an acid. It is often wrongly assumed that
neutralization should result in a solution with pH 7.0, which is only the
case with similar acid and base strengths during a reaction.
Neutralization with a base weaker than the acid results in a weakly
acidic salt. An example is the weakly acidic ammonium chloride,
which is produced from the strong acid hydrogen chloride and the
weak base ammonia. Conversely, neutralizing a weak acid with a
strong base gives a weakly basic salt, e.g. sodium fluoride from
hydrogen fluoride and sodium hydroxide.
Weak acidweak base equilibrium
In order for a protonated acid to lose a proton, the pH of the system must rise above the pK
a
of the acid. The
decreased concentration of H
+
in that basic solution shifts the equilibrium towards the conjugate base form (the
deprotonated form of the acid). In lower-pH (more acidic) solutions, there is a high enough H
+
concentration in
the solution to cause the acid to remain in its protonated form.
Solutions of weak acids and salts of their conjugate bases form buffer solutions.
Applications of acids
There are numerous uses for acids. Acids are often used to remove rust and other corrosion from metals in a
process known as pickling. They may be used as an electrolyte in a wet cell battery, such as sulfuric acid in a
car battery.
Strong acids, sulfuric acid in particular, are widely used in mineral processing. For example, phosphate minerals
react with sulfuric acid to produce phosphoric acid for the production of phosphate fertilizers, and zinc is
produced by dissolving zinc oxide into sulfuric acid, purifying the solution and electrowinning.
In the chemical industry, acids react in neutralization reactions to produce salts. For example, nitric acid reacts
with ammonia to produce ammonium nitrate, a fertilizer. Additionally, carboxylic acids can be esterified with
alcohols, to produce esters.
Acids are used as additives to drinks and foods, as they alter their taste and serve as preservatives. Phosphoric
acid, for example, is a component of cola drinks. Acetic acid is used in day-to-day life as vinegar. Carbonic
acid is an important part of some cola drinks and soda. Citric acid is used as a preservative in sauces and
pickles.
Tartaric acid is an important component of some commonly used foods like unripened mangoes and tamarind.
Natural fruits and vegetables also contain acids. Citric acid is present in oranges, lemon and other citrus fruits.
Oxalic acid is present in tomatoes, spinach, and especially in carambola and rhubarb; rhubarb leaves and unripe
Basic structure of an amino
acid.
carambolas are toxic because of high concentrations of oxalic acid.
Ascorbic acid (Vitamin C) is an essential vitamin for the human body and is present in such foods as amla,
lemon, citrus fruits, and guava.
Certain acids are used as drugs. Acetylsalicylic acid (Aspirin) is used as a pain killer and for bringing down
fevers.
Acids play important roles in the human body. The hydrochloric acid present in the stomach aids in digestion by
breaking down large and complex food molecules. Amino acids are required for synthesis of proteins required
for growth and repair of body tissues. Fatty acids are also required for growth and repair of body tissues.
Nucleic acids are important for the manufacturing of DNA and RNA and transmitting of traits to offspring
through genes. Carbonic acid is important for maintenance of pH equilibrium in the body.
Acid catalysis
Acids are used as catalysts in industrial and organic chemistry; for example, sulfuric acid is used in very large
quantities in the alkylation process to produce gasoline. Strong acids, such as sulfuric, phosphoric and
hydrochloric acids also effect dehydration and condensation reactions. In biochemistry, many enzymes employ
acid catalysis.
[3]
Biological occurrence
Many biologically important molecules are acids. Nucleic acids, which contain
acidic phosphate groups, include DNA and RNA. Nucleic acids contain the
genetic code that determines many of an organism's characteristics, and is
passed from parents to offspring. DNA contains the chemical blueprint for the
synthesis of proteins which are made up of amino acid subunits. Cell
membranes contain fatty acid esters such as phospholipids.
An -amino acid has a central carbon (the or alpha carbon) which is
covalently bonded to a carboxyl group (thus they are carboxylic acids), an
amino group, a hydrogen atom and a variable group. The variable group, also
called the R group or side chain, determines the identity and many of the
properties of a specific amino acid. In glycine, the simplest amino acid, the R group is a hydrogen atom, but in all
other amino acids it is contains one or more carbon atoms bonded to hydrogens, and may contain other
elements such as sulfur, oxygen or nitrogen. With the exception of glycine, naturally occurring amino acids are
chiral and almost invariably occur in the L-configuration. Peptidoglycan, found in some bacterial cell walls
contains some D-amino acids. At physiological pH, typically around 7, free amino acids exist in a charged form,
where the acidic carboxyl group (-COOH) loses a proton (-COO
) and the basic amine group (-NH

2
) gains a
proton (-NH
3
+
). The entire molecule has a net neutral charge and is a zwitterion, with the exception of amino
acids with basic or acidic side chains. Aspartic acid, for example, possesses one protonated amine and two
deprotonated carboxyl groups, for a net charge of 1 at physiological pH.
Fatty acids and fatty acid derivatives are another group of carboxylic acids that play a significant role in biology.
These contain long hydrocarbon chains and a carboxylic acid group on one end. The cell membrane of nearly all
organisms is primarily made up of a phospholipid bilayer, a micelle of hydrophobic fatty acid esters with polar,
hydrophilic phosphate "head" groups. Membranes contain additional components, some of which can participate
in acid-base reactions.
Aspirin (acetylsalicylic acid) is a
carboxylic acid.
In humans and many other animals, hydrochloric acid is a part of the gastric acid secreted within the stomach to
help hydrolyze proteins and polysaccharides, as well as converting the inactive pro-enzyme, pepsinogen into the
enzyme, pepsin. Some organisms produce acids for defense; for example, ants produce formic acid.
Acid-base equilibrium plays a critical role in regulating mammalian breathing. Oxygen gas (O
2
) drives cellular
respiration, the process by which animals release the chemical potential energy stored in food, producing carbon
dioxide (CO
2
) as a byproduct. Oxygen and carbon dioxide are exchanged in the lungs, and the body responds
to changing energy demands by adjusting the rate of ventilation. For example, during periods of exertion the
body rapidly breaks down stored carbohydrates and fat, releasing CO
2
into the blood stream. In aqueous
solutions such as blood CO
2
exists in equilibrium with carbonic acid and bicarbonate ion.
CO
2
+ H
2
O H
2
CO
3
H
+
+ HCO
3
It is the decrease in pH that signals the brain to breathe faster and deeper, expelling the excess CO
2
and
resupplying the cells with O
2
.
Cell membranes are generally impermeable to charged or large, polar
molecules because of the lipophilic fatty acyl chains comprising their
interior. Many biologically important molecules, including a number of
pharmaceutical agents, are organic weak acids which can cross the
membrane in their protonated, uncharged form but not in their
charged form (i.e. as the conjugate base). For this reason the activity
of many drugs can be enhanced or inhibited by the use of antacids or
acidic foods. The charged form, however, is often more soluble in
blood and cytosol, both aqueous environments. When the
extracellular environment is more acidic than the neutral pH within the
cell, certain acids will exist in their neutral form and will be membrane
soluble, allowing them to cross the phospholipid bilayer. Acids that
lose a proton at the intracellular pH will exist in their soluble, charged
form and are thus able to diffuse through the cytosol to their target.
Ibuprofen, aspirin and penicillin are examples of drugs that are weak acids.
Common acids
Mineral acids (inorganic acids)
Hydrogen halides and their solutions: hydrofluoric acid (HF), hydrochloric acid (HCl), hydrobromic acid
(HBr), hydroiodic acid (HI)
Halogen oxoacids: hypochlorous acid (HClO), chlorous acid (HClO
2
), chloric acid (HClO
3
), perchloric
acid (HClO
4
), and corresponding compounds for bromine and iodine
Sulfuric acid (H
2
SO
4
)
Fluorosulfuric acid (HSO
3
F)
Nitric acid (HNO
3
)
Phosphoric acid (H
3
PO
4
)
Fluoroantimonic acid (HSbF
6
)
Fluoroboric acid (HBF
4
)
Hexafluorophosphoric acid (HPF
6
)
Chromic acid (H
2
CrO
4
)
Boric acid (H
3
BO
3
)
Sulfonic acids
Methanesulfonic acid (or mesylic acid, CH
3
SO
3
H)
Ethanesulfonic acid (or esylic acid, CH
3
CH
2
SO
3
H)
Benzenesulfonic acid (or besylic acid, C
6
H
5
SO
3
H)
p-Toluenesulfonic acid (or tosylic acid, CH
3
C
6
H
4
SO
3
H)
Trifluoromethanesulfonic acid (or triflic acid, CF
3
SO
3
H)
Polystyrene sulfonic acid (sulfonated polystyrene, [CH
2
CH(C
6
H
4
)SO
3
H]
n
)
Carboxylic acids
Acetic acid (CH
3
COOH)
Citric acid (C
6
H
8
O
7
)
Formic acid (HCOOH)
Gluconic acid HOCH
2
-(CHOH)
4
-COOH
Lactic acid (CH
3
-CHOH-COOH)
Oxalic acid (HOOC-COOH)
Tartaric acid (HOOC-CHOH-CHOH-COOH)
Halogenated carboxylic acids
Halogenation at alpha position increases acid strength, so that the following acids are all stronger than acetic
acid.
Fluoroacetic acid
Trifluoroacetic acid
Chloroacetic acid
Dichloroacetic acid
Trichloroacetic acid
Vinylogous carboxylic acids
Normal carboxylic acids are the direct union of a carbonyl group and a hydroxy group. In vinylogous carboxylic
acids, a carbon-carbon double bond separates the carbonyl and hydroxyl groups.
Ascorbic acid
Nucleic acids
Deoxyribonucleic acid (DNA)
Ribonucleic acid (RNA)
References
Listing of strengths of common acids and bases (http://www.csudh.edu/oliver/chemdata/data-ka.htm)
IUPAC Gold Book - acid (http://goldbook.iupac.org/A00071.html)
Zumdahl, Chemistry, 4th Edition.
Ebbing, D.D., & Gammon, S. D. (2005). General chemistry (8th ed.). Boston, MA: Houghton Mifflin.
ISBN 0-618-51177-6
Pavia, D.L., Lampman, G.M., & Kriz, G.S. (2004). Organic chemistry volume 1: Organic chemistry
351. Mason, OH: Cenage Learning. ISBN 0-7593-4727-1
External links
Science Aid: Acids and Bases (http://scienceaid.co.uk/chemistry/physical/acidbases.html) Information for
High School students
Curtipot (http://www2.iq.usp.br/docente/gutz/Curtipot_.html): Acid-Base equilibria diagrams, pH
calculation and titration curves simulation and analysis freeware
A summary of the Properties of Acids for the beginning chemistry student
(http://canadaconnects.ca/chemistry/10081/)
The UN ECE Convention on Long-Range Transboundary Air Pollution (http://www.unece.org/env/lrtap/)
Chem 106 Acidity Concepts (http://isites.harvard.edu/fs/docs/icb.topic776365.files/lecture%2017.pdf)
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Categories: Acids Acidbase chemistry
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1. ^ Merriam-Webster's Online Dictionary: acid (http://www.merriam-webster.com/dictionary/acid)
2. ^
a

b

c
Ebbing, D.D., & Gammon, S. D. (2005). General chemistry (8th ed.). Boston, MA: Houghton Mifflin.
ISBN 0-618-51177-6
3. ^ Voet, Judith G.; Voet, Donald (2004). Biochemistry. New York: J. Wiley & Sons. pp. 496500. ISBN 978-0-
471-19350-0.

Acid - Wikipedia, The Free Encyclopedia

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8/8/2014 Acid - Wikipedia, the free encyclopedia

, gives up an electron pair to boron trifluoride to form the product

, where HA represents the acid and A

) and lose a second to form carbonate anion

) and the basic amine group (-NH

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